Dylan Penebre ’01 and Ty Macomber ’02

You’re sitting at the bar of your favorite establishment while the server punches your order into the computer, or the host scans a screen for available seating. Chances are the software running that program was developed by Dylan Penebre ’01 and marketed by Ty Macomber ’02.

In 2011, these two high-energy alums joined forces in Boston to create PointOS, a tech company that provides point of sales and payment solutions for restaurants, bars, and nightclubs. The system handles day-to-day operations for a business, such as tracking orders, assessing inventory, and managing the time clock for employees.

“Restaurateurs need point of sales systems at an affordable price,” Penebre explained. “Our ability to provide that service put us on the map.” That map now includes more than 10,000 customers across the U.S. and a presence in 33 countries around the globe. “We design the software that automates the ordering process for servers and provides the analytics to track data of sales and inventory.”

Penebre and Macomber connected at T-P through varsity football and baseball. Although a day student senior year, Penebre became the fourth roommate in the Barstow triple Macomber shared with Brendan Billone and Joey McElligott. When Penebre moved to Boston in 2007, the first person he called was Macomber. “I needed him to help move the couch into my apartment, and we reconnected from there on.”

In 2010, Penebre and another business partner developed the software concept that laid the groundwork for PointOS. The company started in Penebre’s basement in Newton, MA, and Penebre was recruiting his former teammate before Macomber even knew it. “I knew he would be the salesman we needed to make this company a success,” Penebre said. “My first desk was a pop-up poker table,” joked Macomber.

Both men readily acknowledge that Trinity-Pawling shaped their lives and that the School’s philosophy is woven into the fabric of PointOS. “We even use aspects of the effort system to motivate and reward our employees,” admitted Penebre. Moreover, both believe Trinity-Pawling’s competitive athletics program fuels entrepreneurial hunger. “Starting a company is hard, sales is hard,” said Macomber. “However, T-P taught us that persistent effort yields results.”

“Coming to Trinity-Pawling from a small public school gave me a chance to compete in a wider playing field,” Penebre said. “I met successful alumni who came back to campus and opened my eyes to a greater range of opportunities.” Macomber added, “The effort system trained me to work hard and be ready to learn new things. In software and sales, I always have to be on my toes to stay ahead of the curve.

And the brotherhood? “We fostered a bond at Trinity-Pawling,” Penebre said. “When it gets tough, we rely on each other.” Seems like a solid business philosophy.